Oxcarbazepine | CAS#28721-07-5 | Anticonvulsant drug

MedKoo Cat#: 318398 | Name: Oxcarbazepine

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxcarbazepine is an anticonvulsant drug primarily used in the treatment of epilepsy. There is some evidence for oxcarbazepine as a mood-stabilizing agent and thus, it can be used as add-on therapy for bipolar disorder in patients that have failed or are unable to tolerate approved treatments.

Chemical Structure

Oxcarbazepine

CAS#28721-07-5

Theoretical Analysis

MedKoo Cat#: 318398

Name: Oxcarbazepine

CAS#: 28721-07-5

Chemical Formula: C15H12N2O2

Exact Mass: 252.0899

Molecular Weight: 252.27

Elemental Analysis: C, 71.42; H, 4.79; N, 11.10; O, 12.68

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
1g	USD 750.00	2 Weeks
5g	USD 1,250.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Oxcarbazepine, GP 47680, Timox, Trileptal

IUPAC/Chemical Name

5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide

InChi Key

QZAQRPLWHYVQMM-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H12N2O2/c16-15(18)12-9-10-5-1-3-7-13(10)17(19)14-8-4-2-6-11(12)14/h1-6,8-9H,7H2,(H2,16,18)

SMILES Code

O=C(C1=CC2=CC=CCC2=[N+]([O-])C3=CC=CC=C13)N

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxcarbazepine is a sodium channel blocker.

In vitro activity:

This study examined whether structural analogs of CBZ, oxcarbazepine (OXC), and its active metabolite, monohydroxy derivative (MHD), also potentiate GABA(A) receptor current and aggravate seizures. OXC, MHD, and CBZ were applied at or below therapeutically relevant concentrations, in the range of 1–100 μM (Clinckers et al., 2005). Reproducible GABAA receptor current potentiation by OXC was seen at all concentrations tested and was similar to that obtained with CBZ (Fig. 2). MHD had no effect on GABAA receptor current at 1 or 10 μM, and while there was some potentiation at 100 μM, this was significantly less than that induced by CBZ and OXC. Reference: Epilepsia. 2009 Jan;50(1):83-7. https://pubmed.ncbi.nlm.nih.gov/18717705/

In vivo activity:

Oxcarbazepine treatment after CA (cardiac arrest) significantly increased the survival rate and improved neurological deficit when compared with vehicle-treated rats with CA (survival rates ≥ 63.6 versus 6.5%), showing that oxcarbazepine treatment dramatically protected cerebellar Purkinje cells from ischemia and reperfusion injury induced by CA. The salvation of the Purkinje cells from ischemic injury by oxcarbazepine treatment paralleled a dramatic reduction in 4HNE (an end-product of lipid peroxidation) and increased or maintained the endogenous antioxidant enzymes (SOD1 and SOD2). In brief, this study shows that therapeutic treatment with oxcarbazepine after CA apparently saved cerebellar neurons (Purkinje cells) from CA-induced neuronal death by attenuating oxidative stress and suggests that oxcarbazepine can be utilized as a therapeutic medicine for ischemia and reperfusion brain (cerebellar) injury induced by CA. Reference: Antioxidants (Basel). 2022 Dec 12;11(12):2450. https://pubmed.ncbi.nlm.nih.gov/36552657/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	79.28
	DMF:PBS (pH 7.2) (1:1)	0.5	1.98
	DMSO	19.9	78.89

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 252.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Zheng T, Clarke AL, Morris MJ, Reid CA, Petrou S, O'Brien TJ. Oxcarbazepine, not its active metabolite, potentiates GABAA activation and aggravates absence seizures. Epilepsia. 2009 Jan;50(1):83-7. doi: 10.1111/j.1528-1167.2008.01759.x. Epub 2008 Aug 19. PMID: 18717705. 2. Schmutz M, Brugger F, Gentsch C, McLean MJ, Olpe HR. Oxcarbazepine: preclinical anticonvulsant profile and putative mechanisms of action. Epilepsia. 1994;35 Suppl 5:S47-50. doi: 10.1111/j.1528-1157.1994.tb05967.x. PMID: 8039471. 3. Kim YH, Lee TK, Lee JC, Kim DW, Hong S, Cho JH, Shin MC, Choi SY, Won MH, Kang IJ. Therapeutic Administration of Oxcarbazepine Saves Cerebellar Purkinje Cells from Ischemia and Reperfusion Injury Induced by Cardiac Arrest through Attenuation of Oxidative Stress. Antioxidants (Basel). 2022 Dec 12;11(12):2450. doi: 10.3390/antiox11122450. PMID: 36552657; PMCID: PMC9774942. 4. Kim HI, Lee JC, Kim DW, Shin MC, Cho JH, Ahn JH, Lim SS, Kang IJ, Park JH, Won MH, Lee TK. Hypothermia Induced by Oxcarbazepine after Transient Forebrain Ischemia Exerts Therapeutic Neuroprotection through Transient Receptor Potential Vanilloid Type 1 and 4 in Gerbils. Int J Mol Sci. 2021 Dec 27;23(1):237. doi: 10.3390/ijms23010237. PMID: 35008663; PMCID: PMC8745517.

In vitro protocol:

In vivo protocol:

1. Kim YH, Lee TK, Lee JC, Kim DW, Hong S, Cho JH, Shin MC, Choi SY, Won MH, Kang IJ. Therapeutic Administration of Oxcarbazepine Saves Cerebellar Purkinje Cells from Ischemia and Reperfusion Injury Induced by Cardiac Arrest through Attenuation of Oxidative Stress. Antioxidants (Basel). 2022 Dec 12;11(12):2450. doi: 10.3390/antiox11122450. PMID: 36552657; PMCID: PMC9774942. 2. Kim HI, Lee JC, Kim DW, Shin MC, Cho JH, Ahn JH, Lim SS, Kang IJ, Park JH, Won MH, Lee TK. Hypothermia Induced by Oxcarbazepine after Transient Forebrain Ischemia Exerts Therapeutic Neuroprotection through Transient Receptor Potential Vanilloid Type 1 and 4 in Gerbils. Int J Mol Sci. 2021 Dec 27;23(1):237. doi: 10.3390/ijms23010237. PMID: 35008663; PMCID: PMC8745517.

1: Djukic M, Grewe J, Kunz O, Gross O, Nau R. Hyponatremia in geriatric patients. Z Gerontol Geriatr. 2024 Aug 14. English. doi: 10.1007/s00391-024-02342-z. Epub ahead of print. PMID: 39143233. 2: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Oxcarbazepine. 2024 Aug 15. PMID: 30000302. 3: Yu X, Che F, Zhang X, Yang L, Zhu L, Xu N, Qiu S, Li Y. Clinical and genetic analysis of 23 Chinese children with epilepsy associated with KCNQ2 gene mutations. Epilepsia Open. 2024 Aug 14. doi: 10.1002/epi4.13028. Epub ahead of print. PMID: 39141400. 4: Vita G, Nöhles VB, Ostuzzi G, Barbui C, Tedeschi F, Heuer FH, Keller A, DelBello MP, Welge JA, Blom TJ, Kowatch RA, Correll CU. Systematic Review and Network Meta-Analysis: Efficacy and Safety of Antipsychotics vs Antiepileptics or Lithium for Acute Mania in Children and Adolescents. J Am Acad Child Adolesc Psychiatry. 2024 Aug 9:S0890-8567(24)01316-9. doi: 10.1016/j.jaac.2024.07.920. Epub ahead of print. PMID: 39128561. 5: Comparison Table: Some oral antiseizure medications. Med Lett Drugs Ther. 2024 Aug 5;66(1708):e133-e140. doi: 10.58347/tml.2024.1708b. PMID: 39073881. 6: Drugs for epilepsy. Med Lett Drugs Ther. 2024 Aug 5;66(1708):121-128. doi: 10.58347/tml.2024.1708a. PMID: 39073880. 7: Wei X, Wang W, Yin Q, Li H, Ahmed A, Ullah R, Li W, Jing L. In Vivo Chemical Screening in Zebrafish Embryos Identified FDA-Approved Drugs That Induce Differentiation of Acute Myeloid Leukemia Cells. Int J Mol Sci. 2024 Jul 16;25(14):7798. doi: 10.3390/ijms25147798. PMID: 39063039; PMCID: PMC11277044. 8: Cao L, Chen Y, Lv N, Xu Y, Chen H, Tao L. Clinical study of the effect of 5 kinds of antiepileptic drugs on the postictal state. Epilepsy Behav. 2024 Sep;158:109897. doi: 10.1016/j.yebeh.2024.109897. Epub 2024 Jul 15. PMID: 39013292. 9: Yimenicioğlu S, Ekici A. Hot water epilepsy with alone and spontaneous seizures in childhood. Epilepsy Res. 2024 Sep;205:107418. doi: 10.1016/j.eplepsyres.2024.107418. Epub 2024 Jul 14. PMID: 39003967. 10: Neha KC, Panda PK, Mirza AA, Dhamija P, Sharawat IK. Efficacy of oral sodium chloride in reducing the incidence of hyponatremia in children with epilepsy receiving oxcarbazepine monotherapy: A randomized controlled trial (SCHO Trial). Epilepsy Behav. 2024 Sep;158:109939. doi: 10.1016/j.yebeh.2024.109939. Epub 2024 Jul 12. PMID: 39002272. 11: Sommerfeld-Klatta K, Jiers W, Rzepczyk S, Nowicki F, Łukasik-Głębocka M, Świderski P, Zielińska-Psuja B, Żaba Z, Żaba C. The Effect of Neuropsychiatric Drugs on the Oxidation-Reduction Balance in Therapy. Int J Mol Sci. 2024 Jul 3;25(13):7304. doi: 10.3390/ijms25137304. PMID: 39000411; PMCID: PMC11242277. 12: Müller P, Draguhn A, Egorov AV. Persistent sodium currents in neurons: potential mechanisms and pharmacological blockers. Pflugers Arch. 2024 Jul 5. doi: 10.1007/s00424-024-02980-7. Epub ahead of print. Erratum in: Pflugers Arch. 2024 Jul 24. doi: 10.1007/s00424-024-02995-0. PMID: 38967655. 13: Andrade C. Epilepsy, Antiepileptic Drugs, and Adverse Pregnancy Outcomes, 2: Major Congenital Malformations With Antiepileptic Drug Monotherapy. J Clin Psychiatry. 2024 Jul 3;85(3):24f15432. doi: 10.4088/JCP.24f15432. PMID: 38959494. 14: Chanteux H, MacPherson M, Kramer H, Otoul C, Okagaki T, Rospo C, De Bruyn S, Watling M, Bani M, Sciberras D. Overview of preclinical and clinical studies investigating pharmacokinetics and drug-drug interactions of padsevonil. Expert Opin Drug Metab Toxicol. 2024 Jul 9:1-15. doi: 10.1080/17425255.2024.2373108. Epub ahead of print. PMID: 38932723. 15: Borowicz-Reutt K, Banach M. Chronic Treatment with Oxcarbazepine Attenuates Its Anticonvulsant Effect in the Maximal Electroshock Model in Mice. Int J Mol Sci. 2024 Jun 19;25(12):6751. doi: 10.3390/ijms25126751. PMID: 38928457; PMCID: PMC11203542. 16: Zhang H, Ou Z, Zhang E, Liu W, Hao N, Chen Y, Liu Y, Ye H, Zhou D, Wu X. Efficacy and safety of add-on antiseizure medications for focal epilepsy: A network meta-analysis. Epilepsia Open. 2024 Aug;9(4):1550-1564. doi: 10.1002/epi4.12997. Epub 2024 Jun 18. PMID: 38888005; PMCID: PMC11296132. 17: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Eslicarbazepine. 2024 Jun 15. PMID: 29999698. 18: Benjamin S, Ho JM, Tung J, Dholakia S, An H, Antoniou T, Sanger S, Williams JW Jr. Anticonvulsants in the Treatment of Behavioral and Psychological Symptoms in Dementia: A Systematic Review. Am J Geriatr Psychiatry. 2024 May 16:S1064-7481(24)00333-6. doi: 10.1016/j.jagp.2024.05.004. Epub ahead of print. PMID: 38871629. 19: Khadela A, Dave B, Premal Y, Patel N, Sadhwani D. The Phenytoin Ataxia Enigma Unveiled ''A Case Report''. J Pharm Pract. 2024 Jun 13:8971900241262379. doi: 10.1177/08971900241262379. Epub ahead of print. PMID: 38871356. 20: Pergolizzi JV Jr, LeQuang JA, El-Tallawy SN, Wagner M, Ahmed RS, Varrassi G. An update on pharmacotherapy for trigeminal neuralgia. Expert Rev Neurother. 2024 Aug;24(8):773-786. doi: 10.1080/14737175.2024.2365946. Epub 2024 Jun 13. PMID: 38870050.